Windsor County VT Homes for Sale

• 

  

  

  /37

  $585,000

  • 4 Beds
  • 4 Baths
  • 3,934 Sq Ft

  46 Runnals Rd, White River Junction, VT 05001

  Step into timeless character and modern comfort in this unique 4-bedroom, 4-bathroom home. A thoughtful 1984 expansion preserved the original home's historic core featuring a rare early American beehive oven and three-hearth fireplace, while adding over 3,200 sq. ft. of spacious living and a 1,000 sq. ft. in-law apartment. There’s room for everyone here. The sun-drenched kitchen and dining area

  Cheryl Herrmann RE/MAX Group One Realtors

  46 Runnals Rd, White River Junction, VT 05001
• 

  

  

  /19

  $35,000

  • Land
  • 1.98 Acres
  • $17,677 per Acre

  2-47 E Ash Rd, Plymouth, VT 05056

  Nice building lot within Hawk Resort. Some flat areas with potential westerly views. Electric and high speed internet is at street and there is the option to hook into community septic. Nestled in the scenic lakes region, halfway between Killington and Okemo, Hawk offers a prime location for outdoor enthusiasts. Whether you're hitting the slopes, exploring the trails, or simply enjoying the

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  2-47 E Ash Rd, Plymouth, VT 05056
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  /60

  $1,350,000

  • 11 Beds
  • 11 Baths
  • 6,069 Sq Ft

  86 Main St, Ludlow, VT 05149

  Turnkey Village Inn and Restaurant in the heart of Ludlow, Vt. only steps to Okemo Mountain Ski Resort. This fully furnished and equipped property includes 9 guest rooms with private baths, a 2 bedroom, 2 bathroom owner’s apartment, and a former wine bar/restaurant space ready to relaunch with all FF&E included. Historic charm throughout, wood floors, fireplaces, and original detail-paired with

  John Napier TPW Real Estate

  86 Main St, Ludlow, VT 05149
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  /60

  $200,000

  • Land
  • 6.63 Acres
  • $30,166 per Acre

  00 Vermont 103, Andover, VT 05143

  Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

  Rachael Rogala Lange & Lange

  00 Vermont 103, Andover, VT 05143
• 

  

  

  /41

  $845,000

  • 2 Beds
  • 1.5 Baths
  • 1,714 Sq Ft

  403 Horse Shoe Way, Woodstock, VT 05071

  Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

  Danny Kogut Williamson Group Sothebys Intl. Realty

  403 Horse Shoe Way, Woodstock, VT 05071
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  /60

  $2,395,000

  • 6 Beds
  • 5 Baths
  • 3,645 Sq Ft

  1362 Barnard Rd, Woodstock, VT 05091

  Gilbert’s Hill, the very best of Vermont living - Iconic, 112-acre estate with a storybook history as the first “modern” ski run in the US. Located two miles from the village center of Woodstock, the “prettiest small town in America", experience rural peace with convenient access to great restaurants and shops. Turnkey, fully-restored Vermont farmstead - a picturesque family compound with 7

  Chris Lang

  1362 Barnard Rd, Woodstock, VT 05091
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  /60

  $599,000

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  5100 Route 100, Plymouth, VT 05056

  (Das Grünebergehaus) The Green Mountain House. First time offered on market since 1978. This gorgeous farmhouse, circa 1831, has been lovingly maintained & updated over the current owner's term of ownership. Previously owned by the Coolidge Family. During the years of Calvin Coolidge's presidency this home was used as a guest house for political figures to come & stay while visiting President

  Marni Rieger KW Vermont-Killington

  5100 Route 100, Plymouth, VT 05056
• 

  

  /3

  $59,000

  • Land
  • 3.15 Acres
  • $18,730 per Acre

  1003 Quarry Hill Rd, Rochester, VT 05767

  Undeveloped land parcel ready for you to utilize as a permanent home site or a camp spot. A blank canvas with access by truck or large SUV. Very near the Mountain Biking trail system and easy access onto paved town road. With tree clearing, this property can provide a great view of the Green Mt Range.

  Patricia Harvey Xsell Realty LLC

  1003 Quarry Hill Rd, Rochester, VT 05767
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  /57

  $599,000

  • 3 Beds
  • 3 Baths
  • 2,898 Sq Ft

  354 Grout Rd, Perkinsville, VT 05151

  Stunning contemporary home on 6+ acres. Great proximity to the Upper Valley/RT 91 and only 12 miles to skiing at Okemo! Sit in the panoramic south facing dining room and take in the Black River and local mountain views. Your own Vermont paradise! Quiet dead end road. This 1973 residence has a 2008 addition and has been transformed over the years. Many upgrades and updates, some just completed!

  Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

  354 Grout Rd, Perkinsville, VT 05151
• 

  

  /21

  $225,000

  • 1 Bed
  • 1 Bath
  • 801 Sq Ft

  46A Barrister Dr Unit 205, White River Junction, VT 05001

  Light, bright one bedroom unit on the 1st floor of the Georgian building at Silver Brook Common. 801 sq ft! Recent improvements include new refrigerator, a/c unit, ceiling fan, and window blinds. Condo dues include your heat, hot water, water, sewer, trash service, landscaping, and snow plowing! Laundry room in lower level of the building. Walking distance to Advance Transit bus stop. Just 3

  Jeffrey Batchelder Coldwell Banker LIFESTYLES - Hanover

  46A Barrister Dr Unit 205, White River Junction, VT 05001
• 

  

  /35

  $394,000

  • 3 Beds
  • 2.5 Baths
  • 1,918 Sq Ft

  60 Fletcher Ln, Hartford, VT 05001

  Why go on vacation when you can live the lifestyle every day?Updated Quechee Lakes home is just a quick 7-minute ride to the clubhouse, with year-round resort living right at your doorstep.Step inside to a new kitchen outfitted with Wolf appliances, an updated above code wiring, complemented by tile and wood flooring, and a partially replaced roof for peace of mind. With a newer on-demand

  Gerry Stark RE/MAX Upper Valley

  60 Fletcher Ln, Hartford, VT 05001
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  /33

  $3,945,000

  • 5 Beds
  • 5.5 Baths
  • 8,122 Sq Ft

  5685 Vermont 12, Barnard, VT 05031

  If you’ve been looking for the iconic Vermont home, rarely does an opportunity like this present itself. Welcome to HIGHLAND GLEN, an idyllic Vermont home situated on 12 picturesque acres in the quaint town of Barnard, VT. Upon arrival at Highland Glen, you'll immediately sense the special charm of this property, from the red barn to the mature apple orchard and sugar maples - your eyes will be

  John Snyder Snyder Donegan Real Estate Group

  5685 Vermont 12, Barnard, VT 05031
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  /40

  $685,000

  • 3 Beds
  • 3 Baths
  • 3,589 Sq Ft

  152 Parkview Rd, Springfield, VT 05156

  This beautiful Cape offers a wonderful blend of seclusion and privacy with distant mountain views, to include Okemo Mountain 30 minutes away. The property includes 31.72 acres of lovely meadowlands, woods and a private pond. The woods have several walking paths perfect for casual summer strolls and Winter fun for cross-country skiing and snow-shoeing and close to the VAST network of snowmobile

  Gale Alger Alger Real Estate Agency

  152 Parkview Rd, Springfield, VT 05156
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  /55

  $915,000

  • 3 Beds
  • 3 Baths
  • 2,150 Sq Ft

  509 Church Hill Rd, Wood Stock, VT 05091

  Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

  Carol Wood Williamson Group Sothebys Intl. Realty

  509 Church Hill Rd, Wood Stock, VT 05091
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  /10

  $349,000

  • Land
  • 60 Acres
  • $5,817 per Acre

  911 Waterman Rd, Royalton, VT 05068

  Explore the opportunity of this 60 Acre parcel which is beautifully wooded with awesome mountain view potential. Extensive walking trails throughout the land. Possible development options here or build your private dream retreat. VAST Snowmobile Trails run through the property and the backside of the land abuts the Second Branch of the White River. The land has never been percd for septic. Come

  Marni Rieger KW Vermont-Killington

  911 Waterman Rd, Royalton, VT 05068
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  /10

  $147,500

  • 1 Bed
  • 1 Bath
  • 602 Sq Ft

  789 Ski Tow Rd Unit 3, West Windsor, VT 05037

  Well-maintained Nordic Haus 1BR/BA condo with loft and separate study, ready for new owners. This corner unit has a covered porch, an updated kitchen, and upgraded flooring. Enjoy comfortable, low-maintenance living just steps from Ascutney Outdoors for hiking, biking, skiing, and winter tubing. Minutes from the acclaimed Brownsville Butcher Pantry, with easy access to I-91. This property is

  Danny Kogut Williamson Group Sothebys Intl. Realty

  789 Ski Tow Rd Unit 3, West Windsor, VT 05037
• 

  

  /35

  $495,000

  • 4 Beds
  • 3 Baths
  • 2,470 Sq Ft

  3364 W Woodstock Rd, Woodstock, VT 05091

  Welcome to this lovingly updated antique Cape, set on two open, level acres across from the sparkling Ottauquechee River. Just five minutes from Woodstock Village and perfectly positioned on the west side for quick trips to Killington and Pico, this home makes the ideal Vermont getaway. Inside, you’ll find four comfortable bedrooms and a warm, inviting layout designed for making memories. Gather

  Keri Cole Williamson Group Sothebys Intl. Realty

  3364 W Woodstock Rd, Woodstock, VT 05091
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  /20

  $169,000

  • 1 Bed
  • 1 Bath
  • 200 Sq Ft

  3019 Popple Dungeon Rd, Chester, VT 05143

  Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3019 Popple Dungeon Rd, Chester, VT 05143
• 

  

  /19

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  130 Pleasant St, Cavendish, VT 05142

  This home has served as a primary residence and also as an income-producing rental. While the upper level of this home has three bedrooms, the walk-out lower level of the home has such potential as well.It is currently partially finished and is being used as a family room and for storage. The large deck on the end of the house is perfect for taking in some fresh Vermont air or grilling for

  Tyleen Murray Kelley Real Estate, Inc.

  130 Pleasant St, Cavendish, VT 05142
• 

  

  /30

  $525,000

  • 4 Beds
  • 2 Baths
  • 1,888 Sq Ft

  235 Fox Ln, Hartford, VT 05047

  This inviting bi-level home blends comfort, character, and thoughtful updates in a bright, light-filled setting. Cathedral ceilings with decorative beams create an immediate sense of openness, complemented by hardwood floors throughout the main living space. The open-concept layout is anchored by a dramatic floor-to-ceiling brick fireplace with a handsome wood mantle, ideal for everyday living

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  235 Fox Ln, Hartford, VT 05047
• 

  /2

  $210,000

  • 3,950 Sq Ft

  454 Giddings St, Springfield, VT 05150

  GREAT LOCATION ON THIS 3 FAMILY HOME IDEAL FOR A LIVE IN SITUATION OR AS AN INVESTMENT PROPERTY. PRESENT RENT IS BELOW MARKET AND OFFERS GOOD UPSIDE.

  Don Chabot Town and Country Realty

  454 Giddings St, Springfield, VT 05150
• 

  

  /19

  $115,000

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  1500 Brownsville-Hartland Rd, West Windsor, VT 05089

  Here's a chance to own your own property in West Windsor. This 3/4 +/- acre of land abuts one side up to Beaver Brook and you get views of Mt. Ascutney on the other side. This older mobile home with basement, offers the perfect opportunity for an investor. Restore the homes vintage charm or you could modernize the site with a new mobile unit. This was constructed as a 2-bedroom 1 bath home. One

  Ann Jacques Century 21 Highview Realty

  1500 Brownsville-Hartland Rd, West Windsor, VT 05089
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  /11

  $87,826 New Construction

  • 1 Bed
  • 1 Bath
  • 643 Sq Ft

  23 Cubb Ct, Windsor, VT 05089

  Welcome to 23 Cubb Court, Windsor, VT, where modern comfort meets affordability in Mount Ascutney MHP! This brand-new Redman 25206-58 manufactured home offers 1 bedroom, 1 bathroom, and 643 sq. ft. (13'4"x48) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features energy-efficient

  Kate Barry EXP Realty

  23 Cubb Ct, Windsor, VT 05089
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  /60

  $115,000

  • Land
  • 3.28 Acres
  • $35,061 per Acre

  00 Vt Route 103 N, Chester, VT 05143

  Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life.The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing.

  Rachael Rogala Lange & Lange

  00 Vt Route 103 N, Chester, VT 05143
• 

  

  /31

  $425,000

  • 2 Beds
  • 1 Bath
  • 908 Sq Ft

  1873 Old River Rd, White River Junction, VT 05001

  Super cute, renovated two bedroom home. Detached garage for some extra storage. Only 15 minutes to Dartmouth Hitchcock & Dartmouth College. Being 2.5 acres, there is plenty of room to expand if you wanted to!

  Lyndsey Freeman Quechee Lakes Real Estate Center

  1873 Old River Rd, White River Junction, VT 05001
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  /36

  $349,000

  • Land
  • 10.56 Acres
  • $33,049 per Acre

  0 Valley View Dr, Ludlow, VT 05149

  Elevate Your Lifestyle at Summit Ridge - Tucked away in a private, gated community just minutes from the slopes of Okemo and our Lakes Region, this homesite is the perfect canvas for your mountain dream home. Imagine waking up to panoramic, long-range mountain views in every direction—serenity, space, and stunning scenery, all wrapped into one unbeatable location with 10.56 acres. You're just a

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  0 Valley View Dr, Ludlow, VT 05149
• 

  

  /13

  $1,675,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,837 Sq Ft

  4071 Tichnor Rd Unit 4071, Hartford, VT 05001

  To be built, Mountain Stream at Quechee Lakes seamlessly integrates new construction with the natural beauty of Vermont's premier four-season resort community. Offering over 200 homesites and five distinct home styles, Mountain Stream’s residences feature modern, open layouts, abundant natural light, and soaring ceilings. The exclusive designs establish a commitment to sustainable,

  Richard Higgerson Higgerson & Company

  4071 Tichnor Rd Unit 4071, Hartford, VT 05001
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  /58

  $925,000

  • 4 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  168 Okemo Trailside Extension Unit 21B, Ludlow, VT 05149

  Trailside 21B on Okemo Mountain. Discover the perfect balance of comfort, convenience, and mountain lifestyle in this completely renovated 4-bedroom, 3-bathroom trailside condominium located directly on the Sachem Trail. Offering true ski-in/ski-out access, this home makes it easy to enjoy your time on the slopes and retreat back to a warm, inviting space with quality finishes. The lower level

  Kevin Barnes William Raveis Real Estate Vermont Properties

  168 Okemo Trailside Extension Unit 21B, Ludlow, VT 05149
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  /49

  $68,000

  • 1 Bed
  • 2 Baths
  • 775 Sq Ft

  418 Qtr I Jackson Gore Inn, Ludlow, VT 05149

  Top-Floor 1BR/2BA at Jackson Gore – Sleeps 6, Gorgeous Views, Premium Resort AccessExperience the best of slopeside living with this beautifully appointed 1-bedroom, 2-bathroom top-floor unit at Jackson Gore, Okemo Mountain Resort. Perfectly positioned with incredible valley views and a glimpse of the outdoor heated pool, this residence offers both comfort and convenience, just steps from the

  Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  418 Qtr I Jackson Gore Inn, Ludlow, VT 05149
• 

  

  /17

  $125,000

  • Land
  • 10.3 Acres
  • $12,136 per Acre

  167 Leons Ln, Sharon, VT 05068

  Discover a rare development opportunity tucked away in the Vermont woods. Situated on a quiet, dead-end road, this stunning 10+ acre parcel offers the perfect canvas for your dream mountain sanctuary. The land features a serene mix of deciduous and evergreen trees and slopes upward, offering excellent potential for a home with a walk-out basement. While a rustic cabin shell currently sits on the

  Holly Hall Hall Collins Real Estate Group

  167 Leons Ln, Sharon, VT 05068
• 

  

  /13

  $749,000

  • 11 Beds
  • 6 Baths
  • 6,000 Sq Ft

  23-25 Depot, Ludlow, VT 05149

  Okemo-LudlowUnique commercial property in the center of Ludlow Village. Presently 6 apartment units, plus an 8-bay garage. This property has high visibility and plenty of off-street parking, offering many commercial opportunities.Trustee, seller is a Licensed Real Estate Broker. Siding is asbestos shingle.48 Hours advanced notice needed to show, best times late morning & early

  Frank Ellison Ellison Real Estate, Inc.

  23-25 Depot, Ludlow, VT 05149
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  /58

  $369,000

  • 5 Beds
  • 5 Baths
  • 2,375 Sq Ft

  2335 Main St, Cavendish, VT 05142

  Antique home with space for friends & family to join you for some special Vermont time. Currently set up as a single-family home with five bedrooms & bathrooms, the flow of this house allows for privacy and socializing with the upstairs family room & lower living room. There is an attached barn with potential for finishing too as well as an attached garage for toys or cars. The back entry leads

  Tyleen Murray Kelley Real Estate, Inc.

  2335 Main St, Cavendish, VT 05142
• 

  

  /32

  $279,000

  • Land
  • 10.2 Acres
  • $27,353 per Acre

  00 Parker Ln, Weston, VT 05161

  Great 10.2 Acre Building Lot with state approved 5 bedroom septic! Ready to bring your vision to life - this property has already had the hard work done for you and features a large 4 acre newly created meadow with spring fed pond. Architectural renderings of a potential home design are available to help you imagine the possibilities. With southern exposure, views of the Green Mountains, and

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  00 Parker Ln, Weston, VT 05161
• 

  

  /16

  $250,000

  • 5 Beds
  • 2 Baths
  • 1,728 Sq Ft

  101 Mount Vernon St, Springfield, VT 05156

  Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect

  Christine Lewis Brattleboro Area Realty

  101 Mount Vernon St, Springfield, VT 05156
• 

  

  /48

  $899,000

  • 3 Beds
  • 3 Baths
  • 2,172 Sq Ft

  1269 Howard Hill Rd, Chester, VT 05143

  Discover a truly one-of-a-kind Vermont retreat set on 10 acres of peaceful woodland and open meadow. Originally built as a family-run maple sugar shack, this architect-designed home has been thoughtfully reimagined and newly completed, seamlessly blending rustic charm with contemporary comfort to create a warm and inviting hideaway unlike anything else on the market. Post-and-beam construction,

  Cheyanne Pugliese

  1269 Howard Hill Rd, Chester, VT 05143
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  /11

  $85,000

  • Land
  • 15.68 Acres
  • $5,421 per Acre

  00 E Hill Rd, Andover, VT 05143

  Rooted in along scenic East Hill Road in the bucolic town of Andover, this 16-acre parcel offers a rare opportunity to create your own private haven in one of Southern Vermont’s most peaceful and charming settings. Just minutes from Ludlow and the slopes of Okemo Mountain, this location strikes the perfect balance between quiet countryside and convenient access to skiing, shopping, dining, and

  Daire Gibney Barrett and Valley Associates Inc.

  00 E Hill Rd, Andover, VT 05143
• 

  

  /60

  $1,500,000

  • 10 Beds
  • 12 Baths
  • 7,153 Sq Ft

  1589 Main St, Cavendish, VT 05142

  Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space

  Kevin Barnes William Raveis Real Estate Vermont Properties

  1589 Main St, Cavendish, VT 05142
• 

  

  /60

  $2,495,000

  • 4 Beds
  • 4.5 Baths
  • 6,548 Sq Ft

  657 Town Farm Rd, Ludlow, VT 05149

  61 Acre estate with sweeping views and open fields in Ludlow's prestigious South Hill area. Less than 10 minutes to the Okemo ski area and the Ludlow village amenities, this luxury home has received numerous updates in the last several years.Large updated eat-in country kitchen w/ wood cabinetry, stone countertops and updated stainless steel appliances. A gas fireplace with sitting room

  Andre Menard Mary W. Davis Realtor & Assoc., Inc.

  657 Town Farm Rd, Ludlow, VT 05149
• 

  

  /20

  $149,900

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft

  4351 Vermont 11, Chester, VT 05143

  Almost there! This owner has taken this property to a new level...had the septic discovered and has a report, upgraded the electric entrance and added an EV station, laid flooring, opened up a wall for a much nicer open concept, cleaned and made into a little cottage for skiing, nature loving or just plain home. There are rain barrels for water, let nature fill them up or hire the local water

  Christine Lewis Brattleboro Area Realty

  4351 Vermont 11, Chester, VT 05143
• 

  

  /24

  $646,500

  • Land
  • 37.85 Acres
  • $17,081 per Acre

  0 South Rd, Woodstock, VT 05071

  Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream.About two miles to GMHA and South Woodstock village, one mile to VAST trail.40 minutes to skiing at Killington, less to Okemos. Seven miles into Woodstock Village.

  Matthew Spittle Vermont Horse Country Real Estate

  0 South Rd, Woodstock, VT 05071

Showing Results 161 - 200, Page 5 of 11